Hydroxyamine hydrochloride → 2-Oxo-4,5,5-trimethyl-3-thiazoline oxime

HRID 544381Notes

Reaction equation

HRID 544381 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].[CH3:9][C:10]([S:15][C:16]#[N:17])([CH3:14])[C:11](=O)[CH3:12]>O.C(O)C>[N:2](=[C:16]1[N:17]=[C:11]([CH3:12])[C:10]([CH3:14])([CH3:9])[S:15]1)[OH:3]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 141951652-Methyl-3-oxobutan-2-yl thiocyanate

Product 1

HCID 859972442-Oxo-4,5,5-trimethyl-3-thiazoline oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

8.3 g (0.12 mol) of hydroxylamine hydrochloride are dissolved in 50 ml of water and treated with 10.1 g (0.12 mol) of sodium bicarbonate. This solution (pH 6-7) is added at room temperature while stirring to a solution of 14.3 g (0.1 mol) of 3-methyl-3-thiocyanato-2-butanone in 100 ml of ethanol. The temperature of the mixture rises rapidly to 37° C. The mixture is subsequently stirred for an additional 1 hour and 120 mlof the solvent are distilled off at 50° C. under reduced pressure. The residue is extracted three times with 100 ml of diethyl ether each time and the organic phase is washed with a small amount of water, dried over anhydrous sodium sulfate and concentrated until crystallization begins. After cooling, the crystal slurry is treated with 10 ml of n-hexane. The crystals are filtered off under suction, washed with diethylether/n-hexane (2:1) and dried to yield 2-oxo-4,5,5-trimethyl-3-thiazoline oxime, m.p. 151°-153° C.

Workup

  1. customrises rapidly to 37° C
  2. distillation120 mlof the solvent are distilled off at 50° C. under reduced pressure
  3. extractionThe residue is extracted three times with 100 ml of diethyl ether each time
  4. washthe organic phase is washed with a small amount of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated until crystallization
  7. temperatureAfter cooling
  8. additionthe crystal slurry is treated with 10 ml of n-hexane
  9. filtrationThe crystals are filtered off under suction
  10. washwashed with diethylether/n-hexane (2:1)
  11. customdried

Sources & evidence

ORD record
ord-c903caf11cc644d48d001cbcc7ca7f2b
Source dataset
uspto-grants-1984_05
Patent number
US04450157

Reaction notes

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